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At this point, the Champions League is Real Madrid’s competition, other clubs just play in it. The Spanish giants have won the competition a record 14 times since its inception. They’re the most decorated club in the Champions League but what you may not know is that their current manager is also the most successful in the Champions League. The brilliant Italian Carlo Ancelotti has won four Champions League trophies as a manager two of which he won with Los Blancos. The other two, he won with AC Milan who coincidentally trail Real Madrid as the club with the second most Champions League trophies. As a player, he also won the European trophy twice with AC Milan in 1989 and 1990 making him one of only seven people to have won the trophy both as a player and a manager.
Don Carlo as he is popularly called in Spain did not have a particularly smooth career as a manager. He’s had some ups and downs but he has also had some very big wins as the elite manager that he is. After a knee injury forced him to hang his playing boots, Don Carlo turned to the management side of football. He served as an assistant manager with the Italian national team under his former AC Milan coach Arrigo Sacchi, between 1992 and 1995 reaching the 1994 World Cup final.
He then moved on to manage Serie B side Reggiana in the 1995/96 season and helped them secure a promotion to Serie A in his first season. He left Reggiana at the end of his first season with them to manage Parma, another Serie A side. His time at Parma was not as successful as he was later dismissed at the end of the 1997/98 season.
In February 1999, Ancelotti joined Juventus and was off to a flying start as he won the Intertoto Cup in his first full season with the Biaconeri. Unfortunately, that was the only trophy he would win with Juventus. The Italian lost the Scudetto to Lazio by one point despite having a five-point lead going into the last three games. This drew a lot of criticism from the club and its fans. He was dismissed in the next season after he went trophyless finishing as runner-up again to Roma in the Serie A.
Ancelotti’s managerial career really took off when he joined AC Milan, the club he recorded much success with as a player. He was appointed manager of the Italian football giants in November 2001 after they sacked Fatih Terim following a poor performance. Armed with experience from his previous managerial stints, Ancelotti shook things up at AC Milan and eventually led the Rossoneri to their sixth Champions League title. AC Milan beat Juventus 3-2 on penalties at Old Trafford to clinch the title in 2003 and from there on things only got better.
Ancelotti created the best team of the early 2000s and one of the best in football history through a series of brilliant transfers, tactics, and excellent man management. The players in Ancelotti’s AC Milan would go on to become legends of the game. His team over the years featured the likes of Kaka, Pirlo, Rui Costa, Rivaldo, Cafu, Paolo Maldini, Alessandro Nesta, Filippo Inzaghi, and Andriy Shevchenko all of whom are big names in the world of football.
Ancelotti led AC Milan to the 2005 Champions League final where they famously lost out on penalties to Liverpool after leading 3-0 at halftime. Liverpool equalized in the second half and pushed the match to penalties where they beat AC Milan 3-2. Ancelotti’s Milan would have their revenge in the 2007 Champions League final where they beat Liverpool 2-1 at the Olympic stadium in Athens to clinch the club’s seventh Champions League trophy and Ancelotti’s second as manager. He went on to win the FIFA Club World Cup and the UEFA Super Cup the next season. The legendary AC Milan manager announced his resignation from the club in May 2009 after 423 games as manager.
The next place Ancelotti would record Champions League success was at none other than Real Madrid although, after Milan, he managed Chelsea and PSG. He won the league with both clubs but recorded no Champions League glory. He joined Real Madrid in June 2013 and led them to their 10th Champions League trophy defeating Atletico Madrid 4-1. Delivering Real Madrid’s La Decima, Ancelotti became the second manager after Liverpool’s Bob Paisley to win the Champions League as a manager three times and the only person to have won the competition twice as a player and three times as a coach.
He left Real Madrid in 2015 and took a vacation for a while before he returned to management as Bayern Munich’s Boss in December 2015. He won the domestic league in Germany with Bayern before he returned to Italy to replace Mauricio Sarri at Napoli. After Napoli, Ancelotti returned to the Premier League to manage Everton but his time there was largely uneventful.
Don Carlo returned to the Bernabeu following Zinedine Zidane’s shocking resignation from the club in 2021. He won his fourth Champions League trophy as manager in the 2021/2022 season beating Jürgen Klopp’s Liverpool 1-0. This victory brought Real Madrid their record 14th Champions League trophy and made Ancelotti the manager with the most Champions League trophies.
This season, Ancelotti’s Real Madrid is charging for their 15th Champions League trophy and they have a great chance of winning it after defeating title holders and tournament favorites Man City on penalties in the quarterfinals. Real Madrid is set to face Bayern Munich in the semifinals of the competition and they are the favorites to go through as Bayern is not exactly playing its best football this season. Winning the Champions League this season would cement Don Carlo’s legacy in the competition forever, setting a record that would not be broken any time soon.
The immaculately dressed, cigarette-smoking Italian manager Carlo Ancelotti remains one of the best managers in football who has reached the peak of the sport. He remains the only manager to have won all the top five European Leagues. He will go down as a legend of the game both as a player and a manager.
Do you think Ancelotti’s Real Madrid will win this season’s Champions League?